Synthesis of CCl3-substituted amides, ketones, indenes by intermolecular reactions of -CCl3-enones or -CCl3--hydroxy ketones with various nucleophiles in CF3SO3H.

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Synthesis of CCl3-substituted amides, ketones, indenes by intermolecular reactions of -CCl3-enones or -CCl3--hydroxy ketones with various nucleophiles in CF3SO3H. / Sokolov, Vladislav A.; Bakulina, Olga Yu.; Boyarskaya, Irina A.; Spiridonova, Dar’ya V.; Kryukova, Mariya A.; Vasilyev, Aleksander V.

в: New Journal of Chemistry, Том 50, № 2, 12.01.2026, стр. 1065-1076.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{f6fc4cfbb41f488db7e93aa98b503491,

title = "Synthesis of CCl3-substituted amides, ketones, indenes by intermolecular reactions of -CCl3-enones or -CCl3--hydroxy ketones with various nucleophiles in CF3SO3H.",

abstract = "Intermolecular reactions of 1-aryl-4,4,4-trichloro-3-hydroxybutan-1-ones (β-CCl3-β-hydroxy ketones) or 1-aryl-4,4,4-trichlorobut-2-en-1-ones (β-CCl3-enones) with nucleophiles in Br{\o}nsted superacid CF3SO3H (triflic acid, TfOH) result in various CCl3-substituted compounds in good yields. Reactions with nitriles give rise to CCl3-amides. Reactions with cyclohexane or 1,2,4,5-tetramethylbenzene as hydride ion sources afford products of ionic hydrogenation, namely, saturated CCl3-ketones. Reactions with arenes furnish arylated CCl3-ketones, which may be further cyclized into CCl3-indenes. Plausible reaction mechanisms are discussed based on DFT calculations of electronic, orbital, and electrophilic properties of the intermediate cationic species.",

keywords = "enones, triflic acid, carbocations, electrophilic activation",

author = "Sokolov, {Vladislav A.} and Bakulina, {Olga Yu.} and Boyarskaya, {Irina A.} and Spiridonova, {Dar{\textquoteright}ya V.} and Kryukova, {Mariya A.} and Vasilyev, {Aleksander V.}",

note = "Sokolov V.A., Bakulina O.Yu., Boyarskaya I.A., Spiridonova D.V., Kryukova M.A., Vasilyev A.V. Synthesis of CCl3-substituted amides, ketones, indenes by intermolecular reactions of -CCl3-enones or -CCl3--hydroxy ketones with various nucleophiles in CF3SO3H. New Journal of Chemistry, 2026, V. 50, Iss. 2, P. 1065-1076.",

year = "2026",

month = jan,

day = "12",

doi = "10.1039/d5nj03928b",

language = "English",

volume = "50",

pages = "1065--1076",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

number = "2",

}

RIS

TY - JOUR

T1 - Synthesis of CCl3-substituted amides, ketones, indenes by intermolecular reactions of -CCl3-enones or -CCl3--hydroxy ketones with various nucleophiles in CF3SO3H.

AU - Sokolov, Vladislav A.

AU - Bakulina, Olga Yu.

AU - Boyarskaya, Irina A.

AU - Spiridonova, Dar’ya V.

AU - Kryukova, Mariya A.

AU - Vasilyev, Aleksander V.

N1 - Sokolov V.A., Bakulina O.Yu., Boyarskaya I.A., Spiridonova D.V., Kryukova M.A., Vasilyev A.V. Synthesis of CCl3-substituted amides, ketones, indenes by intermolecular reactions of -CCl3-enones or -CCl3--hydroxy ketones with various nucleophiles in CF3SO3H. New Journal of Chemistry, 2026, V. 50, Iss. 2, P. 1065-1076.

PY - 2026/1/12

Y1 - 2026/1/12

N2 - Intermolecular reactions of 1-aryl-4,4,4-trichloro-3-hydroxybutan-1-ones (β-CCl3-β-hydroxy ketones) or 1-aryl-4,4,4-trichlorobut-2-en-1-ones (β-CCl3-enones) with nucleophiles in Brønsted superacid CF3SO3H (triflic acid, TfOH) result in various CCl3-substituted compounds in good yields. Reactions with nitriles give rise to CCl3-amides. Reactions with cyclohexane or 1,2,4,5-tetramethylbenzene as hydride ion sources afford products of ionic hydrogenation, namely, saturated CCl3-ketones. Reactions with arenes furnish arylated CCl3-ketones, which may be further cyclized into CCl3-indenes. Plausible reaction mechanisms are discussed based on DFT calculations of electronic, orbital, and electrophilic properties of the intermediate cationic species.

AB - Intermolecular reactions of 1-aryl-4,4,4-trichloro-3-hydroxybutan-1-ones (β-CCl3-β-hydroxy ketones) or 1-aryl-4,4,4-trichlorobut-2-en-1-ones (β-CCl3-enones) with nucleophiles in Brønsted superacid CF3SO3H (triflic acid, TfOH) result in various CCl3-substituted compounds in good yields. Reactions with nitriles give rise to CCl3-amides. Reactions with cyclohexane or 1,2,4,5-tetramethylbenzene as hydride ion sources afford products of ionic hydrogenation, namely, saturated CCl3-ketones. Reactions with arenes furnish arylated CCl3-ketones, which may be further cyclized into CCl3-indenes. Plausible reaction mechanisms are discussed based on DFT calculations of electronic, orbital, and electrophilic properties of the intermediate cationic species.

KW - enones

KW - triflic acid

KW - carbocations

KW - electrophilic activation

UR - https://www.mendeley.com/catalogue/fb0fbcd8-e730-3066-96d8-4b71cee29d69/

U2 - 10.1039/d5nj03928b

DO - 10.1039/d5nj03928b

M3 - Article

VL - 50

SP - 1065

EP - 1076

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 2

ER -

ID: 147104762